During President Trump’s first term, he effectively outsourced the task of picking judges to lawyers closely associated with the Federalist Society, a 43-year-old conservative legal group, and Leonard Leo, then its executive vice president.
But in his second term, after some of those judges failed to rule in his favor in cases testing the legality of his policy moves, Mr. Trump has lashed out against the organization. In a lengthy social media post in May, he called Mr. Leo a “sleazebag” who “openly brags how he controls Judges.” The Federalist Society, he said, had given him “bad advice.”
Considering the crowd that assembled earlier this month in Washington for the Federalist Society’s annual lawyers’ convention — including many close allies of Mr. Trump — it was clear that the organization still commands influence.
Dozens of federal judges from across the country attended the event at the Washington Hilton. Justices Brett M. Kavanaugh and Amy Coney Barrett of the Supreme Court spoke at the gala dinner and a third justice, Samuel A. Alito Jr., sat among the crowd of 2,300.
What was less clear was if the organization was ready to fully embrace the hyperaggressive legal views of the president who had empowered it like never before….
Even after his complaint about Mr. Leo’s influence over first-term picks, Mr. Trump has continued to use the Federalist Society’s pipeline of judicial talent. The size of the group’s network means that most qualified, Republican-friendly judicial nominees will have some ties to it. Indeed, out of six nominees to the appellate courts that Mr. Trump has chosen in his second term, five have spoken at a society event, according to its website.
But for a society that claims the Constitution as the uniting force for its varied membership, some longtime allies have warned Mr. Trump’s second term poses an unusual challenge. Actions like killing people suspected of trafficking drugs at sea, ordering up investigations of his political opponents and excoriating judges who rule against him, they say, violate both the letter and spirit of America’s founding document.
“There’s a real tension, from a rule-of-law perspective, between some members of the Federalist Society and the Trump administration,” said Edward Whelan, an attorney who has spoken at dozens of the society’s events, and clerked for Justice Antonin Scalia.
“Good judges will make the hard calls they’re obligated to make without worrying what people will say about them. MAGA-oriented voices say that they want fearless judges — but many of them seem really to want judges who will do Trump’s bidding,” he said….